HCID 18385789, compound → HCID 18385602, compound

HRID 2298341Notes

Reaction equation

HRID 2298341 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](SC)[CH:5]=[CH:4][C:3]=1[C:10]1[O:14][C:13]([CH3:16])([CH3:15])[C:12](=[O:17])[C:11]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O[O:25][S:26]([O-:28])=O.[K+].CO.[CH2:32]1COCC1.O>>[Cl:1][C:2]1[CH:7]=[C:6]([S:26]([CH3:32])(=[O:28])=[O:25])[CH:5]=[CH:4][C:3]=1[C:10]1[O:14][C:13]([CH3:16])([CH3:15])[C:12](=[O:17])[C:11]=1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 3

HCID 18385789HCID 18385789, compoundHCID 21892291Methanol tetrahydrofuran waterHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 18385602HCID 18385602, compound

Procedure

350 mg of 5-{2-chloro-4-(methylthio)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone (Example 387) was dissolved in 75 ml of 1:1:1 methanol/THF/water, to which was added 1.0 g of OXONE. The reaction mixture was stirred at room temperature for 6 hours. The reaction mixture was concentrated in vacuo and the resulting residue was extracted with 25 ml water and ethylacetate (50 ml×3). The organic layer was concentrated in vacuo and was purified by column chromatography (hexane/ethylacetate=3:1) to give 252 mg of 5-{2-chloro-4-(methylsulfonyl)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone as a solid. mp: 89-90° C. NMR: δ1.59 (s, 6H), 3.11 (s, 3H), 7.19 (m, 2H), 7.25 (m, 3H), 7.60 (d, J=8.1 Hz, 1H), 7.87 (dd, J=8.1, 1.8 Hz, 1H), 8.07 (d, J=1.8 Hz, 1H). IR (cm−1): 1701, 1625, 1586, 1391, 1319, 1153.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionthe resulting residue was extracted with 25 ml water and ethylacetate (50 ml×3)
  3. concentrationThe organic layer was concentrated in vacuo
  4. customwas purified by column chromatography (hexane/ethylacetate=3:1)

Sources & evidence

ORD record
ord-417bf81dde7046a1ab971f031a82d8b5
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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